Indole derivatives as antiallergy and antiinflammatory agents

Abstract

Alkoxy substituted indole derivatives as inhibitors of lipoxygenase and useful as antiallergy and antiinflammatory agents.

We claim: 
     
       1. A compound of the formula ##STR4## and the pharmaceutically acceptable salts thereof wherein R 1  is quinoylyl or pyridyl; m is an integer of 1 to 2; Y 1  is hydrogen, or alkyl having one to four carbon atoms; Y 2  is hydrogen, alkyl having one to four carbon atoms, pyridylvinylene, benzoyl or substituted benzoyl where said substituent is methyl, methoxy, chloro, fluoro or trifluoromethyl, benzyl or substituted benzyl wherein said substituent is methyl, methoxy, chloro, fluoro or trifluoromethyl; A is --CH 2  -- or --C(O)--; n is an integer of 0 to 3; and X is hydrogen, alkyl having one to three carbon atoms, pyridyl, hydroxy, thienyl, carboxy, alkoxycarbonyl of two to four carbon atoms, amino, benzyloxycarbonylamino, phenyl or substituted phenyl wherein aid substituent is methyl, carboxy, alkoycarbonyl of two to four carbon atoms, methoxy, fluoro, chloro or trifluoromethyl with the proviso that when A is --C(O)--, n is 1 and when n is 0, X is hydrogen. 
     
     
       2. A compound of claim 1, wherein R 1  is 2-quinolyl; m is 1; Y 2  is hydrogen or alkyl having one to four carbon atoms; and A is --CH 2  --. 
     
     
       3. The compound of claim 2, 1-(3-methoxybenzyl)-5-(2-quinolylmethoxy)indole. 
     
     
       4. The compound of claim 2, 1-(3-picolyl)-5-(2-quinolylmethoxy)indole. 
     
     
       5. The compound of claim 2, 1-(3-[3-pyridyl]-n-propyl)-5-(2-quinolylmethoxy)indole. 
     
     
       6. The compound of claim 2, 3-ethyl-1-(3-picolyl)-2-n-propyl-5-(2-quinolylmethoxy)indole. 
     
     
       7. The compound of claim 2, 1-(3-hydroxypropyl)-5-(2-quinolylmethoxy)indole. 
     
     
       8. The compound of claim 2, 3-(5-[2-quinolylmethoxy]indol-1-yl)propionic acid. 
     
     
       9. The compound of claim 2, 4-([5-(2-quinolylmethoxy)indol-1-yl]methyl)benzoic acid. 
     
     
       10. The compound of claim 2, 1-n-heptyl-5-(2-quinolylmethoxy)indole. 
     
     
       11. A compound of claim 1, wherein R 1  is 2-pyridyl; m is 1; Y 1  and Y 2  are each hydrogen; and A is --CH 2  --. 
     
     
       12. The compound of claim 11, 1-(4-chlorobenzyl)-5-(2-pyridylmethoxy)indole. 
     
     
       13. The compound of claim 1, 1-(3-picolyl)-5-(2-pyridylmethoxy)indole. 
     
     
       14. A method for treating a mammal with an allergic or inflammatory condition which comprises administering to said mammal an antiallergic or antiinflammatory effective amount of a compound according to claim 1. 
     
     
       15. A pharmaceutical composition for the treatment of allergic or inflammatory conditions which comprises an antiallergic or antiinflammatory effective amount of a compound according to claim 1 or its pharmaceutically acceptable salt together with a pharmaceutically acceptable carrier.